Triethylamine → 4-Iodo-3-(naphthalen-2-yloxy)-benzoic acid methyl ester

HRID 379038Notes

Reaction equation

HRID 379038 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1B(O)O.[CH2:25](N(CC)CC)C>C(Cl)Cl>[CH3:25][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([I:11])=[C:2]([O:1][C:13]2[CH:14]=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7368543-Hydroxy-4-iodobenzoic acidHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 539211574-Iodo-3-(naphthalen-2-yloxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxy-4-iodo-benzoic acid acid methyl ester (0.505 g, 1.82 mmol), cupric acetate (0.330 g, 1.82 mmol), 2-naphthylboronic acid (0.625 g, 3.63 mmol) and powdered 4A molecular sieves (0.3 g) in CH2Cl2 (21 mL) was treated with triethylamine (1.27 mL, 9.08 mmol) and stirred at ambient temperature for 18 hr. The reaction mixture was filtered through celite, concentrated to dryness and chromatographed (SiO2, 5-40% EtOAc: hexane) to give the title compound. FAB mass spectrum (M+1) 405.

Workup

  1. filtrationThe reaction mixture was filtered through celite,
  2. concentrationconcentrated to dryness
  3. customchromatographed (SiO2, 5-40% EtOAc: hexane)

Sources & evidence

ORD record
ord-4c3bea01e7014b94b4af9526bf27f2c4
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

Loading…